Shelter Island Vacations
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Where to stay in Shelter Island
Silver Beach
While Silver Beach might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Sunset Beach and Shell Beach.
Find the Best Shelter Island Vacation Packages
Shelter Island Beach Vacation
There's nothing like a Shelter Island vacation to give you a little extra bounce in your step. The sound of rolling surf and the smell of clean ocean air are sure to refresh your mind, body and soul. To be close to the town center on your trip to Shelter Island, find a hotel around Wades Beach (2 kilometers away). If you're planning to stay for a bit, look into our Shelter Island packages. Not only can you save some cash, you'll also have other amazing beaches near you to explore, like Shell Beach and Menhadden Lane Beach.
Shelter Island Hotel Deals
Gurney's Montauk Resort & Seawater Spa
Staff wasn’t friendly, amenities not working, pools were closed, heating system in the room was very loud, made it hard to sleep.
Reviewed on Feb 27, 2026
Montauk Manor
Always such a pleasure at the Manor.
Reviewed on Feb 28, 2026
Pier Blue Inn Old Saybrook - Essex
Not fancy but very cute. Clean. Super nice staff. Cozy, delicious Indian restaurant right next door.
Reviewed on Mar 1, 2026
Discover the most popular places to visit in Shelter Island
Havens House
You can spend an afternoon browsing the exhibits at Havens House during your trip to Shelter Island. Stroll along the area's beaches or simply enjoy its wineries.
